Seymour Rosofsky’s works are scrutinizing glimpses at the surreal and ominous characters that populate Midwestern cities and suburban towns. Many of these figures are at once familiar and recognizable to us: lonely old ladies supping tea in a late night urban cafe, Christmas Santa Claus impersonators in drab, cheap looking suits – holiday cheer with a slice of desperation and humiliation -- grey men in grey bars. They reveal a city and its outer edges (Chicago perhaps) that despite being urban and expansive is also quiet, cold, austere. It’s a city that, unlike New York, does sleep, and Rosofsky’s characters are the ones who face the night.

In the Rosofsky retrospective, Xylophone Solo, currently on display at Corbett vs. Dempsey, we are shown that Rosofsky's process included creating drawings with recurring characters that form the basis of, or operate as addendums to, many of his paintings. The show displays some of these works and their recurring figures, which we come to know like the eccentric locals in our neighborhood. These figures are uncanny – strange yet familiar. The show's catalogue discusses two drawings that refer to Rosofsky's 1966 painting, The Alarm, one with a wheelchair bound man playing the cornet in an empty aquarium, another with two men in wheelchairs, this one rather more rejoiceful and energetic, in the same aquarium. In both versions fish writhe around on the floor as though someone broke the glass tanks behind them. There are other interesting repetitions, too – such as the shadowy figure, cowering in a hat and trenchcoat, who appears in two works from 1969, Two Boys in Ski Masks (Skaters) and Children with Masks in the Zoo II. While representing the darker, shadier elements that populate the recesses of urban environments, this figure also inflects an element of film noir into both works – a Chicago-style gangster from another era reminding us that a city’s past lives leave indelible traces.

Rosofsky was a part of the Monster Roster, a group of Chicago artists that included Nancy Spero, Leon Golub and H.C. Westermann. Like these other artists, Rosofsky’s works oscillate between expressionistic realism and pure surrealism. The work Ski Mask People on Tags Hanging from Trees, for example, is completely surreal, depicting flat paper-like people hanging like car fresheners in a forest while donkeys or hogs march beneath them. It’s rather whimsical and comical, but with an edge of starkness. Others, like Elevator (Ascensaur) and Tea in Subway are very real impressions of city living – tired people embedded in their daily rituals. Rosofsky’s drawings are both lively and lifeless at the same time – colors are often bold but muted, figures are expressive yet stiff like mannequins or Matryoshka dolls.

Two of the most striking pieces are the show’s title work, Xylophone Player, and the awkward and funny Seated Man, Blue Background. The former is a sad muscular monster-like man hunched over a xylophone, playing to himself in an empty room. The latter depicts a man sitting uncomfortably in a chair-cum-throne wearing a makeshift crown. He’s like a bankrupt aristocrat trying, and failing, to maintain a prior existence or a man with delusions of grandeur who has constructed his own alternative world in a ramshackle apartment. Eccentricity, isolation, psychological despair and the excesses and strangeness that arise from it are at the heart of Rosofsky's works.

At first, Keiichi Tanaami’s pop drawings on display in the gallery’s west wing seem like the polar opposite of Rosofsky’s somber little monsters. The Monster Roster (along with the Imagists and the Hairy Who) are traditionally understood as the anti-pop: far too concerned with personal, existential, and emotional content and generally not interested in being disinterested, measured, overly ironic. However, though Tanaami’s work does have the signature elements of U.S. pop art – busty dead-eyed girls, hot dogs, Disney cartoon characters – it’s also much more personal, representing the U.S. from an outsider’s point of view. Tanaami’s drawings are what may result if Lichtenstein’s paintings were remixed together into one drawing, and were less cold and more gregarious, funnier and gratuitous. One depicts a woman in a porno pose giving birth to a Mickey Mouse head, as dancing girls pirouette out of Mickey’s skull. Huge scissors threaten to decapitate Mickey or perhaps just cut the umbilical cord. Another is of a woman climaxing as a hand masturbates her. A hot dog takes the place of her vagina, or maybe it’s the hot dog that is helping her reach orgasm. It's a hilarious comment on the way in which sex can sell anything without even a baseline of nuance. There’s something far more celebratory in Tanaami’s works than is found in most U.S. pop – a kind of fascination with the gross excesses that the U.S. has to offer.

It is the sense of reveling in the macabre that fundamentally connects Tanaami and Rosofsky's visions of the U.S. Indeed, one even begets the other. Tanaami's New York is the centre of capitalist production, of fantasy and commodity consumption, that promises sexy girls, tasty food and entertainment in equal measure. Meanwhile, on the edges of the midwest and in the neighborhoods of Chicago far removed from the city center, eccentrics, dreamers and working people forge out whatever kind of life they can muster.